He was the poster boy for the movement to repeal “don’t ask, don’t tell.” Now Dan Choi is sleeping on a couch, smoking too much weed, watching TED talks and wondering what he’ll do with the rest of his life.

The former chancellor of New York City schools was not, in fact, “a child of the streets. He was not an academically unmotivated student. He did not come from a deprived family background. He did not grow up in public housing as we understand it today.”

In a year when 11 women are running for the U.S. Senate, including six pro-choice Democratic incumbents, the efforts of a group founded by second-wave feminists, named for a first-wave feminist, could once again be a major force in reducing female representation in Congress.

Carl Malamud is on a quest to change the way average citizens can interface with the government – by scanning its paperwork and making it available free online. And he’s financing his effort with his own credit cards.